JP6999550B2 - １，３，４－チアジアゾール化合物およびがんの治療におけるその使用 - Google Patents
１，３，４－チアジアゾール化合物およびがんの治療におけるその使用 Download PDFInfo
- Publication number
- JP6999550B2 JP6999550B2 JP2018526716A JP2018526716A JP6999550B2 JP 6999550 B2 JP6999550 B2 JP 6999550B2 JP 2018526716 A JP2018526716 A JP 2018526716A JP 2018526716 A JP2018526716 A JP 2018526716A JP 6999550 B2 JP6999550 B2 JP 6999550B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- phenyl
- thiadiazole
- mmol
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 0 CCC[C@](CNc1cccnn1)NC(SC(NC([C@@](c1cc(OC(F)(F)I)c(*)cc1)OC)=O)=N)=N Chemical compound CCC[C@](CNc1cccnn1)NC(SC(NC([C@@](c1cc(OC(F)(F)I)c(*)cc1)OC)=O)=N)=N 0.000 description 13
- DQQJBEAXSOOCPG-SSDOTTSWSA-N CC(C)(C)OC(N[C@H]1CNCC1)=O Chemical compound CC(C)(C)OC(N[C@H]1CNCC1)=O DQQJBEAXSOOCPG-SSDOTTSWSA-N 0.000 description 2
- PMPIGCMPRXOOOM-UHFFFAOYSA-N COC(C(OC)=O)c1cc(N(C2)CC2OC)ccc1 Chemical compound COC(C(OC)=O)c1cc(N(C2)CC2OC)ccc1 PMPIGCMPRXOOOM-UHFFFAOYSA-N 0.000 description 2
- NFHGWQLAJYTULJ-UHFFFAOYSA-N CSc1nnccn1 Chemical compound CSc1nnccn1 NFHGWQLAJYTULJ-UHFFFAOYSA-N 0.000 description 2
- HFFQCPIULDZNPH-XNTDXEJSSA-N CC(C)(C)OC(/N=C(\CC1)/CN1c1cccnn1)=O Chemical compound CC(C)(C)OC(/N=C(\CC1)/CN1c1cccnn1)=O HFFQCPIULDZNPH-XNTDXEJSSA-N 0.000 description 1
- HWVZIEOTWRUGJU-SECBINFHSA-N CC(C)(C)OC(N[C@H](CC1)CN1c(nn1)ccc1F)=O Chemical compound CC(C)(C)OC(N[C@H](CC1)CN1c(nn1)ccc1F)=O HWVZIEOTWRUGJU-SECBINFHSA-N 0.000 description 1
- JJRZOYMJIJXTMO-LLVKDONJSA-N CC(C)(C)OC(N[C@H](CC1)CN1c1ccc(C)nn1)=O Chemical compound CC(C)(C)OC(N[C@H](CC1)CN1c1ccc(C)nn1)=O JJRZOYMJIJXTMO-LLVKDONJSA-N 0.000 description 1
- VTNGXGUZRYQGRO-SECBINFHSA-N CC(C)(C)OC(N[C@H](CC1)CN1c1nccnn1)=O Chemical compound CC(C)(C)OC(N[C@H](CC1)CN1c1nccnn1)=O VTNGXGUZRYQGRO-SECBINFHSA-N 0.000 description 1
- VIGDMQJXEAYTCM-UHFFFAOYSA-N CCOC(C(O)=O)c1cc(OC(F)(F)F)ccc1 Chemical compound CCOC(C(O)=O)c1cc(OC(F)(F)F)ccc1 VIGDMQJXEAYTCM-UHFFFAOYSA-N 0.000 description 1
- DERXELLTUOVDQH-UHFFFAOYSA-N CN(C1)CC1F Chemical compound CN(C1)CC1F DERXELLTUOVDQH-UHFFFAOYSA-N 0.000 description 1
- NVBHAFAVARZYFO-UHFFFAOYSA-N CN(C1)CC1OC Chemical compound CN(C1)CC1OC NVBHAFAVARZYFO-UHFFFAOYSA-N 0.000 description 1
- BOCZAEXJISUNCC-UHFFFAOYSA-N COC(C(O)=O)c1cc(N(C2)CC2OC)ccc1 Chemical compound COC(C(O)=O)c1cc(N(C2)CC2OC)ccc1 BOCZAEXJISUNCC-UHFFFAOYSA-N 0.000 description 1
- AKHUQPGHPNBCFW-HNNXBMFYSA-N COC(C1)CN1c(cc(cc1)/C(/C(Nc2nnc(NC[C@H](CC3)CN3c3cccnn3)[s]2)=O)=[O]\C)c1F Chemical compound COC(C1)CN1c(cc(cc1)/C(/C(Nc2nnc(NC[C@H](CC3)CN3c3cccnn3)[s]2)=O)=[O]\C)c1F AKHUQPGHPNBCFW-HNNXBMFYSA-N 0.000 description 1
- HRDQSHNZIPLABL-UHFFFAOYSA-N COCC(C(O)=O)c1cc(OC)ccc1 Chemical compound COCC(C(O)=O)c1cc(OC)ccc1 HRDQSHNZIPLABL-UHFFFAOYSA-N 0.000 description 1
- HRDQSHNZIPLABL-UHFFFAOYSA-M COCC(C([O-])=O)c1cc(OC)ccc1 Chemical compound COCC(C([O-])=O)c1cc(OC)ccc1 HRDQSHNZIPLABL-UHFFFAOYSA-M 0.000 description 1
- BVXKPJNFBXKDMN-FOIQADDNSA-N CO[C@@H](C(Nc1nnc(N[C@H](CC2)CN2c(nn2)ccc2F)[s]1)=O)c1cc(N(C2)CC2OC)ccc1 Chemical compound CO[C@@H](C(Nc1nnc(N[C@H](CC2)CN2c(nn2)ccc2F)[s]1)=O)c1cc(N(C2)CC2OC)ccc1 BVXKPJNFBXKDMN-FOIQADDNSA-N 0.000 description 1
- NSGZZBXIXXUHJV-NVXWUHKLSA-N CO[C@@H](C(Nc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1)=O)c1cc(N(C2)CC2F)ccc1 Chemical compound CO[C@@H](C(Nc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1)=O)c1cc(N(C2)CC2F)ccc1 NSGZZBXIXXUHJV-NVXWUHKLSA-N 0.000 description 1
- YXAREBOYDYNTJH-UTKZUKDTSA-N CO[C@H](C(CCc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1)=O)c1cc(N(C2)CC2F)ccc1 Chemical compound CO[C@H](C(CCc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1)=O)c1cc(N(C2)CC2F)ccc1 YXAREBOYDYNTJH-UTKZUKDTSA-N 0.000 description 1
- WDDBMFLLFAMIRF-INSVYWFGSA-N CO[C@H](C(Nc1nnc(NC(CC2)CN2c2cccnn2)[s]1)=O)c(cc1)cc(OC(F)(F)F)c1F Chemical compound CO[C@H](C(Nc1nnc(NC(CC2)CN2c2cccnn2)[s]1)=O)c(cc1)cc(OC(F)(F)F)c1F WDDBMFLLFAMIRF-INSVYWFGSA-N 0.000 description 1
- MNFRCGGOXJMUGK-BTYIYWSLSA-N CO[C@H](C(Nc1nnc(NC[C@H](CC2)CN2c2cccnn2)[s]1)=O)c1cc(N(C2)CC2I)cc(OC)c1 Chemical compound CO[C@H](C(Nc1nnc(NC[C@H](CC2)CN2c2cccnn2)[s]1)=O)c1cc(N(C2)CC2I)cc(OC)c1 MNFRCGGOXJMUGK-BTYIYWSLSA-N 0.000 description 1
- UMJHPBFCPYNKTO-QRWLVFNGSA-N CO[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2cccnn2)[s]1)=O)c(cc1)cc(N(C2)CC2OC)c1F Chemical compound CO[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2cccnn2)[s]1)=O)c(cc1)cc(N(C2)CC2OC)c1F UMJHPBFCPYNKTO-QRWLVFNGSA-N 0.000 description 1
- GQMGFRGNZPYVQI-UHFFFAOYSA-N COc1cc(C(N=O)=O)cc(OC(F)(F)[IH]C)c1 Chemical compound COc1cc(C(N=O)=O)cc(OC(F)(F)[IH]C)c1 GQMGFRGNZPYVQI-UHFFFAOYSA-N 0.000 description 1
- UTNSGYHPEBNQCN-UHFFFAOYSA-N COc1cc(CO)cc(OC(F)(F)F)c1 Chemical compound COc1cc(CO)cc(OC(F)(F)F)c1 UTNSGYHPEBNQCN-UHFFFAOYSA-N 0.000 description 1
- LSGSLCKXXITHHP-UHFFFAOYSA-N COc1cc(OC(F)(F)F)cc(C=O)c1 Chemical compound COc1cc(OC(F)(F)F)cc(C=O)c1 LSGSLCKXXITHHP-UHFFFAOYSA-N 0.000 description 1
- WMPDAIZRQDCGFH-UHFFFAOYSA-N COc1cccc(C=O)c1 Chemical compound COc1cccc(C=O)c1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 1
- PRORLQAJNJMGAR-UHFFFAOYSA-N Cc(nn1)ccc1Cl Chemical compound Cc(nn1)ccc1Cl PRORLQAJNJMGAR-UHFFFAOYSA-N 0.000 description 1
- MGGFZUWCVPJHDX-MRVPVSSYSA-N Cc1ccc(N(CC2)C[C@@H]2N)nn1 Chemical compound Cc1ccc(N(CC2)C[C@@H]2N)nn1 MGGFZUWCVPJHDX-MRVPVSSYSA-N 0.000 description 1
- QKKGHNNBGPMHPO-SSDOTTSWSA-O NC(SC(N[C@H](CC1)CN1c1nnccc1)=[NH2+])=N Chemical compound NC(SC(N[C@H](CC1)CN1c1nnccc1)=[NH2+])=N QKKGHNNBGPMHPO-SSDOTTSWSA-O 0.000 description 1
- MZIAKXMLWUZVBQ-GVHYBUMESA-N N[C@H](CC1)CN1C1NN=CC=C1 Chemical compound N[C@H](CC1)CN1C1NN=CC=C1 MZIAKXMLWUZVBQ-GVHYBUMESA-N 0.000 description 1
- NKABOLBGITYRPF-ZCFIWIBFSA-N N[C@H](CC1)CN1c(nn1)ccc1F Chemical compound N[C@H](CC1)CN1c(nn1)ccc1F NKABOLBGITYRPF-ZCFIWIBFSA-N 0.000 description 1
- ORTSTWVHFCOGNF-UHFFFAOYSA-N Nc1nnc(NC(C2)C2(CC2)CN2c2nccnn2)[s]1 Chemical compound Nc1nnc(NC(C2)C2(CC2)CN2c2nccnn2)[s]1 ORTSTWVHFCOGNF-UHFFFAOYSA-N 0.000 description 1
- OYTMCYCTANJQCG-LESKNEHBSA-N Nc1nnc(NC(C2)[C@@]2(CC2)CN2c2nnccc2)[s]1 Chemical compound Nc1nnc(NC(C2)[C@@]2(CC2)CN2c2nnccc2)[s]1 OYTMCYCTANJQCG-LESKNEHBSA-N 0.000 description 1
- BDBFPNBOFLDJND-SSDOTTSWSA-N Nc1nnc(N[C@H](CC2)CN2c2cccnn2)[s]1 Chemical compound Nc1nnc(N[C@H](CC2)CN2c2cccnn2)[s]1 BDBFPNBOFLDJND-SSDOTTSWSA-N 0.000 description 1
- XIVHDNOVZMYPBY-ZCFIWIBFSA-N Nc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1 Chemical compound Nc1nnc(N[C@H](CC2)CN2c2nccnn2)[s]1 XIVHDNOVZMYPBY-ZCFIWIBFSA-N 0.000 description 1
- JAODGCQHDICTKX-UHFFFAOYSA-N OCc1cc(C2COC2)ccc1 Chemical compound OCc1cc(C2COC2)ccc1 JAODGCQHDICTKX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562260789P | 2015-11-30 | 2015-11-30 | |
| US62/260,789 | 2015-11-30 | ||
| PCT/EP2016/079250 WO2017093299A1 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018535986A JP2018535986A (ja) | 2018-12-06 |
| JP2018535986A5 JP2018535986A5 (https=) | 2020-01-16 |
| JP6999550B2 true JP6999550B2 (ja) | 2022-02-10 |
Family
ID=57485461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526716A Active JP6999550B2 (ja) | 2015-11-30 | 2016-11-30 | １，３，４－チアジアゾール化合物およびがんの治療におけるその使用 |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US10323028B2 (https=) |
| EP (1) | EP3383873B1 (https=) |
| JP (1) | JP6999550B2 (https=) |
| KR (1) | KR20180083942A (https=) |
| CN (1) | CN108349966B (https=) |
| AR (1) | AR106874A1 (https=) |
| AU (1) | AU2016363718B2 (https=) |
| BR (1) | BR112018010806A2 (https=) |
| CA (1) | CA3005495C (https=) |
| CL (1) | CL2018001407A1 (https=) |
| CO (1) | CO2018006928A2 (https=) |
| EA (1) | EA201891241A1 (https=) |
| ES (1) | ES2914333T3 (https=) |
| IL (1) | IL259510A (https=) |
| MX (1) | MX2018006532A (https=) |
| NI (1) | NI201800064A (https=) |
| PH (1) | PH12018501131A1 (https=) |
| RU (1) | RU2018123714A (https=) |
| SG (1) | SG11201803810XA (https=) |
| SV (1) | SV2018005702A (https=) |
| TN (1) | TN2018000127A1 (https=) |
| TW (1) | TW201733587A (https=) |
| WO (1) | WO2017093299A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| TW201731511A (zh) * | 2015-11-30 | 2017-09-16 | 阿斯特捷利康公司 | １，３，４-噻二唑化合物及其在治療癌症中之用途 |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US9938265B2 (en) | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| ES2903182T3 (es) * | 2017-06-13 | 2022-03-31 | Medshine Discovery Inc | Compuesto como inhibidor GLS1 |
| AU2019363115B2 (en) | 2018-10-16 | 2021-12-09 | Medshine Discovery Inc. | Thiadiazole derivative and uses thereof as a GLS1 inhibitor |
| WO2025196446A1 (en) * | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014533699A (ja) | 2011-11-21 | 2014-12-15 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | グルタミナーゼのヘテロ環式阻害剤 |
| WO2015101957A2 (en) | 2014-01-06 | 2015-07-09 | Rhizen Pharmaceuticals Sa | Novel glutaminase inhibitors |
| JP2019501134A (ja) | 2015-11-30 | 2019-01-17 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | １，３，４−チアジアゾール化合物および癌の治療におけるその使用 |
| JP6538830B2 (ja) | 2014-05-30 | 2019-07-03 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | １，３，４−チアジアゾール化合物および癌を治療する際のその使用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| BR112015010955A2 (pt) * | 2012-11-16 | 2017-07-11 | Calithera Biosciences Inc | inibidores de glutaminase heterocíclica |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| EP3116872A4 (en) * | 2014-03-14 | 2017-08-30 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| TW201731511A (zh) | 2015-11-30 | 2017-09-16 | 阿斯特捷利康公司 | １，３，４-噻二唑化合物及其在治療癌症中之用途 |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
-
2016
- 2016-11-29 US US15/363,030 patent/US10323028B2/en active Active
- 2016-11-29 TW TW105139337A patent/TW201733587A/zh unknown
- 2016-11-30 CA CA3005495A patent/CA3005495C/en active Active
- 2016-11-30 WO PCT/EP2016/079250 patent/WO2017093299A1/en not_active Ceased
- 2016-11-30 JP JP2018526716A patent/JP6999550B2/ja active Active
- 2016-11-30 TN TNP/2018/000127A patent/TN2018000127A1/en unknown
- 2016-11-30 EP EP16806028.3A patent/EP3383873B1/en active Active
- 2016-11-30 CN CN201680067245.3A patent/CN108349966B/zh active Active
- 2016-11-30 SG SG11201803810XA patent/SG11201803810XA/en unknown
- 2016-11-30 EA EA201891241A patent/EA201891241A1/ru unknown
- 2016-11-30 AR ARP160103663A patent/AR106874A1/es unknown
- 2016-11-30 AU AU2016363718A patent/AU2016363718B2/en active Active
- 2016-11-30 KR KR1020187018472A patent/KR20180083942A/ko not_active Withdrawn
- 2016-11-30 ES ES16806028T patent/ES2914333T3/es active Active
- 2016-11-30 RU RU2018123714A patent/RU2018123714A/ru not_active Application Discontinuation
- 2016-11-30 MX MX2018006532A patent/MX2018006532A/es unknown
- 2016-11-30 BR BR112018010806A patent/BR112018010806A2/pt not_active Application Discontinuation
-
2018
- 2018-05-22 IL IL259510A patent/IL259510A/en unknown
- 2018-05-24 CL CL2018001407A patent/CL2018001407A1/es unknown
- 2018-05-29 PH PH12018501131A patent/PH12018501131A1/en unknown
- 2018-05-29 SV SV2018005702A patent/SV2018005702A/es unknown
- 2018-05-29 NI NI201800064A patent/NI201800064A/es unknown
- 2018-06-29 CO CONC2018/0006928A patent/CO2018006928A2/es unknown
-
2019
- 2019-05-03 US US16/402,825 patent/US10981904B2/en active Active
-
2021
- 2021-04-15 US US17/231,164 patent/US11753405B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014533699A (ja) | 2011-11-21 | 2014-12-15 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | グルタミナーゼのヘテロ環式阻害剤 |
| WO2015101957A2 (en) | 2014-01-06 | 2015-07-09 | Rhizen Pharmaceuticals Sa | Novel glutaminase inhibitors |
| JP6538830B2 (ja) | 2014-05-30 | 2019-07-03 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | １，３，４−チアジアゾール化合物および癌を治療する際のその使用 |
| JP2019501134A (ja) | 2015-11-30 | 2019-01-17 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | １，３，４−チアジアゾール化合物および癌の治療におけるその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108349966A (zh) | 2018-07-31 |
| JP2018535986A (ja) | 2018-12-06 |
| SG11201803810XA (en) | 2018-06-28 |
| TW201733587A (zh) | 2017-10-01 |
| US10323028B2 (en) | 2019-06-18 |
| TN2018000127A1 (en) | 2019-10-04 |
| KR20180083942A (ko) | 2018-07-23 |
| CL2018001407A1 (es) | 2018-10-12 |
| AU2016363718A1 (en) | 2018-07-12 |
| WO2017093299A1 (en) | 2017-06-08 |
| AR106874A1 (es) | 2018-02-28 |
| SV2018005702A (es) | 2018-11-27 |
| RU2018123714A (ru) | 2020-01-09 |
| EP3383873B1 (en) | 2022-03-09 |
| MX2018006532A (es) | 2019-05-15 |
| NI201800064A (es) | 2018-10-18 |
| IL259510A (en) | 2018-07-31 |
| BR112018010806A2 (pt) | 2018-11-27 |
| EP3383873A1 (en) | 2018-10-10 |
| CA3005495C (en) | 2023-12-12 |
| CN108349966B (zh) | 2022-02-15 |
| EA201891241A1 (ru) | 2019-01-31 |
| US11753405B2 (en) | 2023-09-12 |
| US10981904B2 (en) | 2021-04-20 |
| CO2018006928A2 (es) | 2018-10-10 |
| AU2016363718B2 (en) | 2019-11-14 |
| CA3005495A1 (en) | 2017-06-08 |
| US20170152255A1 (en) | 2017-06-01 |
| US20190389853A1 (en) | 2019-12-26 |
| PH12018501131A1 (en) | 2019-01-21 |
| US20210246131A1 (en) | 2021-08-12 |
| ES2914333T3 (es) | 2022-06-09 |
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